CN110551015B - Compound and organic light-emitting element using same - Google Patents

Compound and organic light-emitting element using same Download PDF

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CN110551015B
CN110551015B CN201910444867.9A CN201910444867A CN110551015B CN 110551015 B CN110551015 B CN 110551015B CN 201910444867 A CN201910444867 A CN 201910444867A CN 110551015 B CN110551015 B CN 110551015B
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organic light
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CN110551015A (en
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韩美连
许瀞午
洪性佶
李东勋
尹喜敬
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LG Chem Ltd
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Abstract

The present invention provides a novel compound and a method for producing the sameAn organic light emitting device, the novel compound being represented by chemical formula 1, chemical formula 2 or chemical formula 3, wherein in chemical formula 1, chemical formula 2 and chemical formula 3, X is O or S, M is an alkali metal or an alkaline earth metal, Z is O or S, Y is CH or N, L is O, S, CO, SO2、
Figure DDA0002073287540000011
Or
Figure DDA0002073287540000012
A is benzene, naphthalene or pyridine, B is benzene or pyridine, R are all hydrogen, or two of R together form a single bond and the remainder are hydrogen, and compounds
Figure DDA0002073287540000013
Excluded from the chemical formula 1.
Figure DDA0002073287540000014

Description

Compound and organic light-emitting element using same
Technical Field
The present invention relates to a novel compound and an organic light emitting device including the same.
Background
In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting element, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to the ground state.
As for organic materials used for the organic light emitting element as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
The present invention relates to a novel compound and an organic light emitting device including the same.
The present invention provides a compound represented by the following chemical formula 1, chemical formula 2 or chemical formula 3:
[ chemical formula 1]
Figure GDA0003558776130000021
In the chemical formula 1 described above,
x is O or S, and X is O or S,
m is an alkali metal or an alkaline earth metal,
y is a group of CH or N,
l is O, S, CO, SO2、
Figure GDA0003558776130000022
Figure GDA0003558776130000023
A is benzene, naphthalene or pyridine,
b is benzene or pyridine, and the content of the benzene or pyridine,
all of R are hydrogen, or 2 of R together form a single bond and the rest are hydrogen, wherein the following compounds are excluded from the above chemical formula 1,
Figure GDA0003558776130000024
[ chemical formula 2]
Figure GDA0003558776130000031
In the chemical formula 2 as described above,
x is O or S, and X is O or S,
m is an alkali metal or an alkaline earth metal,
z is O or S, and the compound is a linear or branched compound,
[ chemical formula 3]
Figure GDA0003558776130000032
In the chemical formula 3 above, the first and second,
x is O or S, and X is O or S,
m is an alkali metal or an alkaline earth metal,
y is CH or N.
In addition, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron injection layer, and the electron injection layer includes a compound represented by chemical formula 1, chemical formula 2, or chemical formula 3.
The compound represented by chemical formula 1, chemical formula 2, or chemical formula 3 described above may be used as a material of an organic layer of an organic light emitting element in which improvement in efficiency, lower driving voltage, and/or improvement in lifetime characteristics can be achieved. In particular, the above-described compound represented by chemical formula 1, chemical formula 2, or chemical formula 3 may be used as an electron injecting material.
Drawings
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 4.
Description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light-emitting layer 8: electron transport layer
9: electron injection layer
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
In the context of the present specification,
Figure GDA0003558776130000041
represents a bond to other substituents.
The term "substituted or unsubstituted" as used herein means a compound selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, and an alkylthio group(s) ((R))
Figure GDA0003558776130000042
Alkyl thio), arylthio(s) ((R)
Figure GDA0003558776130000043
Figure GDA0003558776130000044
Aryl thio), alkylsulfonyl(s) ((s)
Figure GDA0003558776130000045
Alkyl sulfoxy), arylsulfonyl (C)
Figure GDA0003558776130000046
Aryl sulfo xy), silyl, boryl, alkyl, cycloalkyl, alkenyl, Aryl, aralkylOne or more substituents selected from the group consisting of an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group containing at least one of N, O and S atoms, or a substituent formed by connecting at least 2 substituents selected from the above-mentioned substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
Figure GDA0003558776130000051
In the ester group, in the present specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
Figure GDA0003558776130000052
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
Figure GDA0003558776130000053
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-nonyl group, a 2, 2-dimethylheptyl group, a 1-ethyl-propyl group, a 1, 1-dimethyl-propyl group, a, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
Figure GDA0003558776130000061
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the compound may be
Figure GDA0003558776130000071
And so on. But is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure GDA0003558776130000072
Azolyl group,
Figure GDA0003558776130000073
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazino-pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoquinoxalyl, pyrazinyl, pyrazino-pyrimidinyl, triazinyl, pyridopyrimidinyl, pyrazino-yl, benzoxazolyl, and a
Figure GDA0003558776130000074
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Figure GDA0003558776130000075
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group can be applied to the above description of the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, the heteroarylene group is a 2-valent group, and in addition to this, the above description about the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
Preferably, the above chemical formula 1 is any one selected from the following chemical formulas:
Figure GDA0003558776130000081
in the above formula, X, M and Y are as defined above.
Preferably, M is Li.
Representative examples of the compound represented by the above chemical formula 1, chemical formula 2 or chemical formula 3 are as follows:
Figure GDA0003558776130000091
Figure GDA0003558776130000101
in addition, as an example, when M is Li, the present invention provides a method for producing the compounds represented by the following chemical formulas 1 'and 2' as the following reaction formulas 1 and 2, and the remaining compounds can be produced by a similar method, but is not limited to this method.
[ reaction formula 1]
Figure GDA0003558776130000102
[ reaction formula 2]
Figure GDA0003558776130000103
In the above reaction formulae 1 and 2, the definition of each substituent is the same as that described above.
The above reaction formulas 1 and 2 are reactions for reacting a starting material with an organolithium compound (organolithium agent). The organolithium compound that can be used in the above reaction can be appropriately selected according to the compound to be produced, and tert-butyllithium can be used as an example. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
In addition, the present invention provides an organic light emitting element including the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3. As an example, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron injection layer, and the electron injection layer includes a compound represented by chemical formula 1, chemical formula 2, or chemical formula 3.
The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic light emitting element according to the present invention may be an organic light emitting element having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting element according to the present invention may be an inverted (inverted) type organic light emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure example of an organic light emitting element according to an embodiment of the present invention is shown in fig. 1 and 2.
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3 may be included in the above electron injection layer.
The organic light emitting element according to the present invention may be manufactured by materials and methods well known in the art, except that the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3 is included in the above electron injection layer. In addition, when the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting element according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.
In addition, when the compound represented by chemical formula 1, chemical formula 2, or chemical formula 3 is used to manufacture an organic light-emitting device, the organic layer may be formed not only by a vacuum evaporation method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting element can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function so that holes can be smoothly injected into the organic layer. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; gold such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), etcA metal oxide; such as ZnO, Al or SnO2A combination of a metal such as Sb and an oxide; such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; such as LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect with respect to the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The luminescent material is capable of receiving holes and electrons from the hole transport layer and the electron transport layer, respectivelyThe substance that emits light in the visible light region by binding them is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo [ b ]
Figure GDA0003558776130000133
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. As the host material, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Figure GDA0003558776130000131
Figure GDA0003558776130000132
Pyrimidine derivatives, and the like, but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styrene amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,
Figure GDA0003558776130000134
Diindenopyrene and the like, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and the styrylamine compound is substituted with one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylaminoUnsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons from the cathode well and transfer the electrons to the light emitting layer, and a substance having a high electron mobility is preferable. Specific examples thereof include an Al complex of 8-hydroxyquinoline and an Al complex containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The organic light emitting element according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type depending on the material used.
In addition, the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.
The production of the compound represented by the above chemical formula 1, chemical formula 2 or chemical formula 3 and the organic light emitting element comprising the same is specifically described in the following examples. However, the following examples are illustrative of the present invention, and the scope of the present invention is not limited thereto.
[ examples ]
Example 1: production of Compound 1
Figure GDA0003558776130000141
Under a stream of nitrogen, (2-hydroxyphenyl) (phenyl) methanone (15g,75.7mmol) was added to anhydrous THF solvent and cooled to-78 deg.C. When the temperature of the solution reached-78 deg.C, a solution of tert-butyllithium (2.5M in hexane) (30.3mL,75.7mmol) was slowly added dropwise. Then, the temperature was slowly raised to room temperature, and the mixture was stirred for 2 hours. After completion of the reaction, the solvent was distilled off to solidify, and then purified with ethanol, whereby compound 1(8.5g, yield 55%) was obtained.
MS：[M+H]+＝205
Example 2: production of Compound 2
Figure GDA0003558776130000142
Compound 2 was produced by the same method as the production method of compound 1, except that (2-mercaptophenyl) (phenyl) methanone was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝221
Example 3: production of Compound 3
Figure GDA0003558776130000151
Compound 3 was produced by the same method as the production method of compound 1, except that (2-hydroxypyridin-3-yl) (phenyl) methanone was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝206
Example 4: production of Compound 4
Figure GDA0003558776130000152
Compound 4 was produced by the same method as the production method of compound 1, except that 2- (phenylsulfonyl) phenol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝241
Example 5: production of Compound 5
Figure GDA0003558776130000153
Compound 5 was produced by the same method as the production method of compound 1, except that 3- (phenylsulfonyl) pyridine-2-thiol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝258
Example 6: production of Compound 6
Figure GDA0003558776130000154
Compound 6 was produced by the same method as the production method of compound 1, except that (2-hydroxyphenyl) (naphthalen-2-yl) methanone was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝255
Example 7: production of Compound 7
Figure GDA0003558776130000161
Compound 7 was produced by the same method as the production method of compound 1, except that 1-hydroxy-9H-fluoren-9-one was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝203
Example 8: production of Compound 8
Figure GDA0003558776130000162
Compound 8 was produced by the same method as the production method of compound 1, except that dibenzo [ b, d ] furan-4-thiol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝207
Example 9: production of Compound 9
Figure GDA0003558776130000163
Compound 9 was produced by the same method as the production method of compound 1, except that benzo [4,5] thieno [2,3-b ] pyridin-8-ol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝208
Example 10: production of Compound 10
Figure GDA0003558776130000171
Compound 10 was produced by the same method as the production method of compound 1, except that (2-mercaptopyridin-3-yl) diphenylphosphine oxide was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝208
Example 11: production of Compound 11
Figure GDA0003558776130000172
Compound 11 was produced by the same method as the production method of compound 1, except that 5- (2-hydroxypyridin-3-yl) benzo [ b ] phosphoindole 5-oxide was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝300
Example 12: production of Compound 12
Figure GDA0003558776130000173
Compound 12 was produced by the same method as the production method of Compound 1, except that 5- (2-thiophenyl) benzo [ b ] phosphoindole 5-sulfide was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝331
Example 13: production of Compound 13
Figure GDA0003558776130000174
Compound 13 was produced by the same method as the production method of compound 1, except that 4-hydroxy-5-phenylbenzo [ b ] phosphoindole 5-oxide was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝299
Example 14: production of Compound 14
Figure GDA0003558776130000181
Compound 14 was produced by the same method as the production method of compound 1, except that 1-hydroxy-9-phenylphosphide [2,3-c ] pyridine 9-oxide was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝300
Example 15: production of Compound 15
Figure GDA0003558776130000182
Compound 15 was produced by the same method as the production method of compound 1, except that 6- (2-hydroxyphenyl) dibenzo [ c, e ] [1,2] oxaphosphorine 6-oxide was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝315
Example 16: production of Compound 16
Figure GDA0003558776130000183
Compound 16 was produced by the same method as the production method of compound 1, except that indolo [3,2,1-jk ] carbazol-9-ol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝264
Example 17: production of Compound 17
Figure GDA0003558776130000191
Compound 17 was produced by the same method as the production method of compound 1, except that indolo [3,2,1-jk ] carbazole-9-thiol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝280
Example 18: preparation of Compound 18
Figure GDA0003558776130000192
Compound 18 was produced by the same method as the production method of compound 1, except that naphtho [1,2-b ] benzofuran-1-ol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝241
Example 19: production of Compound 19
Figure GDA0003558776130000193
Compound 19 was produced by the same method as the production method of compound 1, except that benzo [ b ] naphtho [2,1-d ] thiophen-1-ol was used instead of (2-hydroxyphenyl) (phenyl) methanone.
MS：[M+H]+＝257
[ Experimental example ]
Experimental example 1
Will be provided with
Figure GDA0003558776130000194
The glass substrate coated with ITO (indium tin oxide) is put into distilled water dissolved with detergent,washing was performed by ultrasonic waves. At this time, the detergent was prepared by Fischer Co, and the distilled water was filtered twice by a Filter (Filter) manufactured by Millipore Co. The ITO was washed for 30 minutes and then twice with distilled water to perform ultrasonic washing for 10 minutes. After the completion of the distilled water washing, the resultant was ultrasonically washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared
Figure GDA0003558776130000201
The following compound HAT was thermally vacuum-deposited to form a hole injection layer. Vacuum evaporating the following compound NPB on the hole injection layer to
Figure GDA0003558776130000202
The thickness of (2) forms a hole transport layer. On the hole transport layer, the following compound HT-A and
Figure GDA0003558776130000203
the electron blocking layer is formed by vacuum evaporation to a thickness of (3). The following compound BH and the following compound BD are vacuum-evaporated on the electron blocking layer at a weight ratio of 25:1 to obtain
Figure GDA0003558776130000204
The thickness of (a) forms a light emitting layer. The following compound ET-a and the compound 1 produced in mutexample 1 were vacuum-evaporated on the light-emitting layer at a weight ratio of 1:1 to obtain
Figure GDA0003558776130000205
Forming a first electron transport layer. The following compound ET-B and lithium Li (lithium) are vacuum-evaporated on the first electron transport layer at a weight ratio of 100:1 to obtain
Figure GDA0003558776130000206
Forming a second electron transport layer. On the second electron transport layer
Figure GDA0003558776130000207
Aluminum is deposited to form a cathode.
Figure GDA0003558776130000208
In the above process, the evaporation speed of the organic material is maintained
Figure GDA0003558776130000209
Aluminum maintenance
Figure GDA00035587761300002010
The vacuum degree is maintained at 1X 10 during the vapor deposition-7～5×10-8And (4) supporting to manufacture the organic light-emitting element.
Experimental examples 2 to 19
Organic light-emitting elements were produced in the same manner as in the above experimental examples, except that compounds described in table 1 below were used instead of compound 1.
Comparative Experimental examples 1 to 5
Organic light-emitting elements were produced in the same manner as in the above experimental examples, except that compounds described in table 1 below were used instead of compound 1. In table 1 below, compounds Liq, EIL a, EIL B, EIL C, and EIL D are as follows, respectively.
Figure GDA0003558776130000211
The organic light-emitting elements manufactured in the above experimental examples and comparative experimental examples were applied with 10mA/cm2The driving voltage and the luminous efficiency were measured by applying 20mA/cm2The time (T90) until the luminance became 90% of the initial luminance was measured. The results are shown in table 1 below.
[ TABLE 1]
Figure GDA0003558776130000221

Claims (3)

1. An organic light emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron injection layer containing a compound represented by the following chemical formula:
Figure FDA0003558776120000011
in the chemical formula, in the formula,
x is O or S, and the compound is shown in the specification,
m is an alkali metal, and M is an alkali metal,
y is a group of CH or N,
wherein, the following compounds are excluded,
Figure FDA0003558776120000012
2. the organic light-emitting element according to claim 1, wherein M is Li.
3. An organic light emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron injection layer, and the electron injection layer includes any one compound selected from the following compounds:
Figure FDA0003558776120000021
Figure FDA0003558776120000031
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Cobalt(III)-Catalyzed [5 + 1] Annulation for 2H-Chromenes Synthesis via Vinylic C-H Activation and Intramolecular Nucleophilic Addition;Kuppusamy, Ramajayam等;《American Chemical Society》;20161231;第6卷(第6期);3909-3913 *

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